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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 10, 1980 - Issue 11
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Original Articles

Conjugate Addition of Alkyllithium Reagents to α,β-Unsaturated N, N',N'-Trimethylhydrazides

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Pages 837-842 | Published online: 06 Dec 2006
 

Abstract

The site of nucleophilic attack by an alkyllithium reagent upon an α,β-unsaturated carbonyl compound is governed by, among other factors, the nature of the group attached to the carbonyl.1 Thus the amount of carbonyl addition decreases in favor of conjugate addition for the α,β-unsaturated series: aldehyde, ketone, ester, amide. We wish to report that α,β-unsaturated carboxylic acid trimethylhydrazides, which have an exceptionally unreactive carbonyl group2, undergo exclusive conjugate addition with simple alkyllithium reagents.3 Furthermore, the derived hydrazide lithium enolates can be transformed in convenient and useful ways.

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